29883-15-6 Usage
Description
Amygdalin, also known as a cyanogenic glycoside, is a primary reference substance with assigned absolute purity derived from seeds of plants in the Rosaceae family, such as bitter almonds, peach, and apricot pits. It has diverse biological activities, including anti-inflammatory and experimental antineoplastic properties. Amygdalin is characterized by its white fine crystalline powder appearance and is classified as a toxic substance.
Uses
Used in Pharmaceutical Applications:
Amygdalin is used as an experimental antineoplastic agent for its potential anti-cancer properties. It has been found to induce cell cycle arrest at the G0/G1 phase, decrease cyclin A and Cdk2 levels, and inhibit cell growth in certain bladder cancer cells when used at specific concentrations.
Used in Enzyme Research:
Amygdalin serves as a substrate to identify, differentiate, and characterize enzymes such as maltase(s), emulsin(s), and β-glucosidase(s), contributing to the understanding of these enzymes' functions and applications.
Used in Anti-inflammatory Applications:
Amygdalin is used for its anti-inflammatory properties, which may help in reducing inflammation in various conditions.
Used in Cardiovascular Applications:
In vivo, amygdalin has been shown to reduce triglyceride, total cholesterol, and LDL levels, as well as aortic sinus plaque area in an LDLR-/mouse model of atherosclerosis. This suggests its potential use in managing and treating cardiovascular diseases.
Used in Inflammation and Immune Response Applications:
Amygdalin has demonstrated the ability to reduce the production of pro-inflammatory cytokines (TNF-α, IL-1β, and IL-6) and decrease neutrophil and macrophage infiltration in bronchoalveolar lavage fluid (BALF) in a mouse model of LPS-induced acute lung injury. This indicates its potential use in managing inflammatory and immune response-related conditions.
Uses and Synthetic Methods of Amygdalin
Amygdalin is a β-cyano-glycoside in the bitter almond that is bound to cyano (CN), which releases free cyano groups after eating the bitter almond, so that the food is poisoned. Amygdalin is a product of the metabolism of phenylalanine in the bitter almond. Amygdalin has β-glucosidase and amygdalinase (oxynitrilase): the former catalyzed amygdalin into two molecules of glucose and one molecule of amygdalenone through hydrolysis; the later catalyzes mandelonitrile into almond nitrile cyanide (HCN) and benzaldehyde through hydrolysis. Amygdalin exists in seeds, such as almonds.
Many plant root cells contain glycosides, with no toxic effect when in sugar type. Glycosides hydrolysis produce toxic substances leading to cell death. Mandelic glycosides contained in peach root is a glycoside. Amylose hydrolysis produce two kinds of plant toxins-hydrogen cyanide and benzaldehyde. Peeling root lesion formation and necrosis occurred in the vicinity of the stabbed nematode but not in contact zone; in addition, in vitro tests have proved that the pratylenchus penetrans can make amygdalin hydrolysis.
As a cyanide containing glucoside, it can be used as a substrate for such as maltase, almond casein and β-glucosidase identification, differentiation and characterization.
Toxicity classification
Highly toxic
Acute toxicity
Acute toxicity Oral-Rat LD50: 522 mg/kg; Oral-mouse LD50: 443 mg/kg
Flammability Hazardous properties
Combustible; producing toxic nitrogen oxides when heated.
Storage and transportation
Ventilation, low temperature, drying
Fire extinguishing agent
Dry powder, foam, sand, carbon dioxide
World Health Organization (WHO)
Laetrile, which consists mainly of amydgalin, a glycoside
extracted from the kernels of apricots, peaches and other fruits, has been available
for over 30 years in preparations purporting to be beneficial in the treatment of
cancer. Although there is no evidence that these are efficacious, preparations
continued to be widely used and, until the late 1970s, they were considered to be
harmless. However, oral dosage forms, which may be broken down in the gut to
hydrogen cyanide, have subsequently been shown to be potentially lethal. This has
resulted in restrictive regulatory measures in several countries.
Biochem/physiol Actions
Cyanogenic glycoside that is a component of bitter almonds and apricot pits. There is no scientific evidence that amygdalin itself is an effective anti-cancer agent. Recent studies using β?glucoside linked to a tumor-associated monoclonal antibody to release cyanide at the tumor cell has shown significant cytotoxicity.
Safety Profile
Human poison by ingestion(infant data). Poison experimentally by ingestion. Anexperimental teratogen. Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.
Purification Methods
D-Amygdalin recrystallises from water as the trihydrate, or from EtOH. It is present in bitter almonds. [Smith Chem Ber 64 1115 1931, Beilstein 17/8 V 188.]
Check Digit Verification of cas no
The CAS Registry Mumber 29883-15-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,9,8,8 and 3 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 29883-15:
(7*2)+(6*9)+(5*8)+(4*8)+(3*3)+(2*1)+(1*5)=156
156 % 10 = 6
So 29883-15-6 is a valid CAS Registry Number.
InChI:InChI=1/C20H27NO11/c21-6-10(9-4-2-1-3-5-9)30-20-18(28)16(26)14(24)12(32-20)8-29-19-17(27)15(25)13(23)11(7-22)31-19/h1-5,10-20,22-28H,7-8H2/t10-,11+,12+,13+,14+,15-,16-,17+,18+,19+,20+/m0/s1
29883-15-6Relevant articles and documents
Synthesis and Biological Evaluation of Cyanogenic Glycosides
Yashunsky, Dmitry V.,Kulakovskaya, Ekaterina V.,Kulakovskaya, Tatiana V.,Zhukova, Olga S.,Kiselevskiy, Mikhail V.,Nifantiev, Nikolay E.
, p. 460 - 474 (2015/12/23)
An efficient procedure for the synthesis of cyanogenic glycosides with different carbohydrate units was developed. Amygdalin (3), prunasin (1), sambunigrin (2), and neoamygdalin (21) were prepared according to the elaborated method, and biological tests, including antifungal, antibacterial, and cytotoxic activities, were performed.
Study on the Prevention of Racemization of Amygdalin
Takayama, Yuzi,Kawai, Satoshi
, p. 778 - 781 (2007/10/02)
Studies were conducted to find suitable conditions for the prevention of racemization of amygdalin in aqueous solution.Evaluation of racemization was carried out by determination of the ratios of neoamygdalyn and amygdalin using a capillary gas chromatographic technique.Racemization of amygdalin in aqueous solution was accelerated by increases on pH and temperature, but racemization was low below pH 3.0 even with heating.Ascorbic acid is useful as an acidification reagent for the suppression of racemization, and has the added clinical benefit of vitamin C activity.Keywords - amygdalin; isoamygdalin separation; racemization; racemizati on prevention; capillary gas chromatography
